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Intramolecular nucleophilic and electrophilic cyclization of N- alkyne-substituted pyrrole esters is described. Efficient routes towards the synthesis of pyrrolopyrazinone, pyrrolotriazinone and pyrrolooxazinone have been developed. First, N -alkyne-substituted pyrrole ester derivatives were synthesized. Introduction of various substituents into the alkyne functionality was accomplished by a copper-catalyzed cross-coupling reaction. Nucleophilic cyclization of N -alkyne-substituted methyl 1 H -pyrrole-2-carboxylates with hydrazine afforded the 6- exo -dig/6- endo- dig cyclization products depending on the electronic nature of the substituents attached to the alkyne. On the other hand, cyclization of N -alkyne-substituted methyl 1 H -pyrrole-2-carboxylates with iodine only resulted in the formation of the 6- endo -dig cyclization product regardless of the substitution of the alkyne functionality.

beilstein journal of organic chemistry

Nucleophilic and electrophilic cyclization of <i>N</i>-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties

Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties